4-乙基-3,5-二甲基-1H-吡咯-2-甲酸乙酯 | 2199-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-乙基-3,5-二甲基-1H-吡咯-2-甲酸乙酯
• 英文名称: ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate
• 英文别名: ethyl 3,5-dimethyl-4-ethyl-1H-pyrrole-2-carboxylate；ethyl 4-ethyl-3,5-dimethylpyrrole-2-carboxylate；2,4-dimethyl-3-ethyl-5-ethoxycarbonylpyrrole；2-ethoxycarbonyl-3,5-dimethyl-4-ethylpyrrole；2-carboethoxy-4-ethyl-3,5-dimethylpyrrole；2-carbethoxy-4-ethyl-3,5-dimethylpyrrole；ethyl 4-ethyl-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 2199-47-5
• 化学式: C₁₁H₁₇NO₂
• mdl: MFCD00030376
• 分子量: 195.261
• InChiKey: GIGBRYTXWUHNAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  306.7±30.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 储存条件：
  储存温度应维持在2-8°C，需密封并保持干燥。

SDS

Name:	Ethyl 4-ethyl-3 5-dimethyl-1h-pyrrole-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	2199-47-5

Section 1 - Chemical Product MSDS Name:Ethyl 4-ethyl-3 5-dimethyl-1h-pyrrole-2-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2199-47-5	Ethyl 4-ethyl-3,5-dimethyl-1H-pyrrole-	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2199-47-5: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 87 - 88 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H17NO2
Molecular Weight: 195

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2199-47-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-ethyl-3,5-dimethyl-1H-pyrrole-2-carboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 2199-47-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2199-47-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2199-47-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-乙基-3,5-二甲基-1H-吡咯-2-甲酸乙酯 在 甲酸 、 氢溴酸 作用下， 反应 4.0h， 以79.9%的产率得到2,4,8,10-tetramethyl-3,9-diethyldipyrrolyl-5,7-methene
  参考文献：
  名称：

  用于 Zn2+ 离子定量检测和表达分析的二吡咯亚甲基发色荧光化学传感器

  摘要：

  合成了二吡咯亚甲基衍生物作为用于定量检测和表达分析 Zn 2+离子的新型发色荧光化学传感器，并对其进行了结构表征。通过紫外-可见光和荧光光谱、摩尔比图和 DFT 计算来评估二吡咯甲烯对Zn 2+的传感过程。由于[ZnL 2 ]配合物的形成，Zn(AcO) 2与二吡咯亚甲基在DMF溶液中的络合伴随着电子吸收光谱中显着的红移和增色效应。在吸收和理论研究的基础上提出了 1:2 (Zn:HL) 结合模式。Zn(AcO) 2的络合常数(lg K o )dipyrromethenes 为 8.1 到 10.9，这意味着 dipyrromethenes 作为 Zn 2+ 的选择性化学传感器的潜力。首次表明六甲基取代的二吡咯亚甲基可以通过由 Zn 2+引起的显着（近 100 倍）“关-开”荧光响应识别DMF 溶液中的Zn 2+离子，并且可见颜色从黄色变为亮绿色在由 [ZnL 2 ]形成诱导的紫外线照射下。六甲基取代的二吡咯亚甲基对

  DOI：

  10.1016/j.molliq.2021.117834
• 作为产物：
  描述：

  ethyl 3,5-dimethyl-4-vinyl-1H-pyrrole-2-carboxylate 在 乙醇 、 镍 作用下， 生成 4-乙基-3,5-二甲基-1H-吡咯-2-甲酸乙酯
  参考文献：
  名称：

  Nicolaus et al., Annali di Chimica, 1956, vol. 46, p. 793,800

  摘要：

  DOI：

文献信息

• Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines
  作者：Balu D. Dherange、Patrick Q. Kelly、Jordan P. Liles、Matthew S. Sigman、Mark D. Levin

  DOI：10.1021/jacs.1c06287

  日期：2021.8.4

  calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is

  在这里，我们报告了一种反应，该反应通过将芳基羰基阳离子等价物分别插入吡咯和吲哚核心选择性地产生 3-芳基吡啶和喹啉基序。通过使用 α-chlorodiazirines 作为相应氯卡宾的热前体，可以修改作为母体 Ciamician-Denstedt 重排核心的传统基于卤仿的协议，以直接提供 3-（杂）芳基吡啶和喹啉。通过氧化可商购的脒鎓盐可方便地在一个步骤中制备氯二氮嗪。检测了作为吡咯取代模式函数的选择性，并提出了基于空间效应的预测模型，DFT 计算支持确定选择性的环丙烷化步骤。计算出人意料地表明，环丙烷化的立体化学对随后形成吡啶核心的电环开环几乎没有影响，这是由于补偿性同芳族稳定化抵消了轨道控制的扭矩选择性效应。通过喹啉的制备和药学相关吡咯的骨架编辑进一步证明了这种骨架转化的效用。
• Alkylation process
  申请人：Canadian Patents & Development Limited

  公开号：US04070366A1

  公开（公告）日：1978-01-24

  Substituted pyrrole compounds, such as 3-ethyl-4-methyl-5-carbethoxy pyrrole, 2,4-dimethyl-3-acetyl pyrrole and 2-methyl-5-carboxy pyrrole-4-propionic acid diethyl ester, are alkylated in a single step by reaction with an aldehyde or ketone in the presence of both an acid condensing agent such as hydriodic acid and a compatible reducing agent such as metallic zinc or stannous chloride. Suitable carbonyl reactants include formaldehyde, paraldehyde, isobutyraldehyde, acetone, cyclohexanone and methyl-isobutyl ketone. This application is a continuation application of U.S. application Ser. No. 281,624 filed Aug. 18, 1972, now abandoned, which is a continuation-in-part application of U.S. application Ser. No. 832,001, filed June 10, 1969, now abandoned.

  取代吡咯类化合物，如3-乙基-4-甲基-5-羰基乙酸酯吡咯、2,4-二甲基-3-乙酰基吡咯和2-甲基-5-羧基吡咯-4-丙酸二乙酯，可通过与醛或酮在存在酸性缩合剂（如碘化氢）和兼容的还原剂（如金属锌或氯化亚锡）的情况下进行一步反应进行烷基化。适合的羰基反应物包括甲醛、对甲醛、异丁醛、丙酮、环己酮和甲基异丁基酮。本申请是美国1972年8月18日申请的第281,624号专利申请的继续申请，该专利申请已被放弃，是美国1969年6月10日申请的第832,001号专利申请的续展部分申请。
• Thermochemistry of substituted pyrroles
  作者：M. V. Berezin、A. S. Semeikin、A. I. V'yugin、G. A. Krestov

  DOI：10.1007/bf00698428

  日期：1993.3

  The heats of solution of a series of substituted pyrroles in benzene, carbon tetrachloride, chloroform, DMF, and pyridine were measured by a calorimetric method at 298.15 K. The influence of substituents in the pyrrole molecule on the energy parameters of solvation by organic solvents is discussed.

  一系列取代的吡咯在苯、四氯化碳、氯仿、DMF和吡啶中的溶解热在298.15 K下通过量热法测量。吡咯分子中的取代基对有机溶剂溶剂化能量参数的影响为讨论。
• ¹⁵N NMR Chemical Shifts for the Identification of Dipyrrolic Structures
  作者：Tabitha E. Wood、Bob Berno、Cory S. Beshara、Alison Thompson

  DOI：10.1021/jo0524932

  日期：2006.4.1

  complexes exhibit chemical shifts around −170 ppm. The presence of electron-withdrawing substituents on one of the pyrrolic rings of dipyrromethenes affects the chemical shifts of both of the nitrogen nuclei in the molecule. Boron difluoride complexes of meso-unsubstituted dipyrromethenes display 15N chemical shifts around −190 ppm. Two examples of free-base dipyrromethenes bearing substituents at the meso-position

  已经制备了多种二吡咯甲烷和二吡咯烷酮，并通过与1 H NMR信号进行二维相关性测定了它们的15 N NMR化学位移。相对于硝基甲烷，在五个二吡咯甲烷实例中的氮原子始终表现出约-231 ppm的化学位移。七个未取代的亚甲基吡啶酮氢溴酸盐的氢溴酸盐实例始终显示15N的化学位移约为-210 ppm，而它们相应的锌（II）络合物的化学位移约为-170 ppm。在二吡咯烷酮的一个吡咯环上存在吸电子取代基会影响分子中两个氮核的化学位移。内消旋取代的吡啶酮的二氟化硼配合物在-190 ppm处显示15 N化学位移。在介孔位置带有取代基的游离碱二吡咯烷酮的两个例子在约-156 ppm处显示15 N化学位移，而对于这些化合物的锌配合物，在-162 ppm处显示。可测量的单键氮氢耦合常数始终在-96 Hz的范围内。自测15N个化学位移具有与结构相关的如此高的规律性，它们可以用作鉴定二吡咯化合物结构的诊断指标。
• Substituted Pyrroles
  作者：N. Mamardashvili、M. Kluyeva、O. Golubchicov

  DOI：10.3390/50100089

  日期：——

  A stepwise synthesis of a-unsubstituted pyrroles with desired substituents in the b-positions of the ring has been devised.

  已设计出一种逐步合成α-未取代吡咯的方案，以便在环的β位引入所需的取代基。